Since stepping into the spotlight over three decades ago, Justin Timberlake has faced his fair share of controversies.
From being arrested on charges of DWI to Nipplegate, keep scrolling for a list of the singer’s most headline-making scandals.
Britney Spears Drama
Justin Timberlake struggled with ‘real drinking problem’ for years, was ‘in a very dark place’: sources
Justin Timberlake arrested on DWI-related charges, refused breathalyzer test and seen leaving court
Justin Timberlake had ‘bloodshot’ eyes, insisted he drank only ‘one martini’ before DWI arrest: police
Timberlake was 18 when he struck up a romance with pop star Britney Spears.
But after their relationship fizzled out three years later, the singer suggested in his hit song “Cry Me a River” that Spears had cheated on him.
Two decades later, the “Toxic” singer flipped the script on Timberlake when she accused him of cheating on her a “couple” of times in her tell-all memoir, “The Woman In Me.”
Janet Jackson Super Bowl Halftime Show
Timberlake sparked backlash again in 2004 after he exposed Janet Jackson’s right breast while performing together during the Super Bowl XXXVIII Halftime Show.
Although the nudity was shown for less than one second, over 140 million people were watching at the time, which resulted in a whopping 540,000 complaints to the FCC.
Timberlake later claimed the incident — dubbed “Nipplegate” — was “unintentional.” However, he did not face any consequences.
Meanwhile, Jackson’s career took a serious hit afterward.
Infidelity
Timberlake allegedly cheated on now-wife Jessica Biel in 2010 with Olivia Munn.
Nine years later, he was spotted getting cozy with “Palmer” co-star Alisha Wainwright at a bar — despite still being married to Biel.
DWI Arrest
In June 2024, Timberlake was arrested on charges of DWI in Sag Harbor, NY. A source told Pvnew at the time that the “Trolls” voice actor was pulled over after having dinner with friends at the historic American Hotel.
